Facile Synthesis of 2'-Deoxy-3'-keto- and 2'-Deoxypseudouridine Derivatives and Analogues. Palladium(II)-Mediated Coupling Reactions of Furanoid Glycals

Article abstract of DOI:10.1021/jo00366a003

C-Nucleosides, of either α or β configuration, are formed selectively in a palladium-mediated coupling reaction between furanoid glycals and (1.3-dimethyl-2,4-dioxo-1,3-dihydropyrimidin-5-yl)mercuric acetate.Control of anomeric configuration is accomplished by suitable choice of substituents for glycal 3-O- and 5-O-hydroxy groups; attack of organopalladium reagent and glycosidic bond formation occurs on the least sterically hindered face of the glycal ring.Removal of substituents from the coupled products yielded 2'-deoxy-3'-keto C-nucleosides, which upon metal hydride reduction produced the corresponding 2'-deoxy C-nucleosides.